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2000 fused pyridine derivatives fused pyridine derivatives R 0450 04 - 170 Synthesis of Enantiopure Oxoindolo-quinolizines. — Reaction of chiral tetrahydrocarbolines (I) and (V) with diketene (II) proceeds by introduction of a dioxobutyl group at the pyridine nitrogen atom. Cyclization to (6S)-methoxycarbonyl or (6S)-hydroxymethyl substituted oxoindoloquino- lizines (IV) and (VII), resp., is then achieved under acidic conditions (2M HCl). On similar ways, the (6S)-carboxy and (6S)-carbamoyl analogues are obtained. Screening of their anticancer activity indicates a significant influence of 6-substituent on the biological activity and provides the best results for 6-methoxycarbonyl derivative (IV). — (ZHAO, MING; WANG, CHAO; GUO, MIN; PENG, SHIQI; WINTERFELDT, EKKEHARD; J. Prakt. Chem. 341 (1999) 7, 677-684; Sch. Pharm. Sci., Beijing Med. Univ., Beijing 100083, Peop. Rep. China; EN) 1

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Page 1: ChemInform Abstract: Synthesis of Enantiopure Oxoindolo-quinolizines

2000 fused pyridine derivatives

fused pyridine derivativesR 0450

04 - 170Synthesis of Enantiopure Oxoindolo-quinolizines. — Reactionof chiral tetrahydrocarbolines (I) and (V) with diketene (II) proceeds byintroduction of a dioxobutyl group at the pyridine nitrogen atom. Cyclizationto (6S)-methoxycarbonyl or (6S)-hydroxymethyl substituted oxoindoloquino-lizines (IV) and (VII), resp., is then achieved under acidic conditions (2MHCl). On similar ways, the (6S)-carboxy and (6S)-carbamoyl analogues areobtained. Screening of their anticancer activity indicates a significant influenceof 6-substituent on the biological activity and provides the best results for6-methoxycarbonyl derivative (IV). — (ZHAO, MING; WANG, CHAO; GUO,MIN; PENG, SHIQI; WINTERFELDT, EKKEHARD; J. Prakt. Chem. 341(1999) 7, 677-684; Sch. Pharm. Sci., Beijing Med. Univ., Beijing 100083, Peop.Rep. China; EN)

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